Literature DB >> 22195730

A stereoselective synthesis of (-)-viridiofungin A utilizing a TiCl(4)-promoted asymmetric multicomponent reaction.

Arun K Ghosh1, Jorden Kass.   

Abstract

A stereoselective synthesis of (-)-viridiofungin A is described. The convergent synthesis utilized a unique highly diastereoselective multicomponent reaction between optically active phenyldihydrofuran and an α-ketoester to provide two chiral centers including a quarternary carbon center in a single step. Other key steps include an acyloxycarbonium ion-mediated tetrahydrofuran ring-opening reaction and a Julia-Kocienski olefination.
© 2011 American Chemical Society

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Year:  2011        PMID： 22195730      PMCID： PMC3262899          DOI： 10.1021/ol203093g

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  12 in total

1.  Highly diastereoselective synthesis of modified nucleosides via an asymmetric multicomponent reaction.

Authors:  Arun K Ghosh; Jorden Kass
Journal:  Chem Commun (Camb)       Date:  2010-01-25       Impact factor: 6.222

2.  Asymmetric multi-component reactions: convenient access to acyclic stereocenters and functionalized cyclopentenoids.

Authors:  Arun K Ghosh; Sarang S Kulkarni; Chun-Xiao Xu; Khriesto Shurrush
Journal:  Tetrahedron Asymmetry       Date:  2008-05-01

3.  A simple, short, and flexible synthesis of viridiofungin derivatives.

Authors:  Stephen M Goldup; Christopher J Pilkington; Andrew J P White; Andrew Burton; Anthony G M Barrett
Journal:  J Org Chem       Date:  2006-08-04       Impact factor: 4.354

4.  Viridiofungins, novel inhibitors of sphingolipid synthesis.

Authors:  S M Mandala; R A Thornton; B R Frommer; S Dreikorn; M B Kurtz
Journal:  J Antibiot (Tokyo)       Date:  1997-04       Impact factor: 2.649

5.  Antimicrobial activity of viridiofungins.

Authors:  J C Onishi; J A Milligan; A Basilio; J Bergstrom; J Curotto; L Huang; M Meinz; M Nallin-Omstead; F Pelaez; D Rew; M Salvatore; J Thompson; F Vicente; M B Kurtz
Journal:  J Antibiot (Tokyo)       Date:  1997-04       Impact factor: 2.649

6.  Asymmetric multicomponent reactions: diastereoselective synthesis of substituted pyrrolidines and prolines.

Authors:  Arun K Ghosh; Sarang Kulkarni; Chun-Xiao Xu; Phillip E Fanwick
Journal:  Org Lett       Date:  2006-09-28       Impact factor: 6.005

7.  Total synthesis of viridiofungin A.

Authors:  Kenji Morokuma; Keisuke Takahashi; Jun Ishihara; Susumi Hatakeyama
Journal:  Chem Commun (Camb)       Date:  2005-03-09       Impact factor: 6.222

8.  TiCl4-promoted multicomponent reaction: a new entry to functionalized alpha-amino acids.

Authors:  Arun K Ghosh; Chun-Xiao Xu; Sarang S Kulkarni; Donald Wink
Journal:  Org Lett       Date:  2005-01-06       Impact factor: 6.005

9.  Novel synthesis of 2-oxo-3-butynoates by copper-catalyzed cross-coupling reaction of terminal alkynes and monooxalyl chloride.

Authors:  Minjie Guo; Dao Li; Zhaoguo Zhang
Journal:  J Org Chem       Date:  2003-12-26       Impact factor: 4.354

10.  Asymmetric synthesis of anti-aldol segments via a nonaldol route: synthetic applications to statines and (-)-tetrahydrolipstatin.

Authors:  Arun K Ghosh; Khriesto Shurrush; Sarang Kulkarni
Journal:  J Org Chem       Date:  2009-06-19       Impact factor: 4.354
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  4 in total

1.  A concise synthetic route to the stereotetrad core of the briarane diterpenoids.

Authors:  Nicholas G Moon; Andrew M Harned
Journal:  Org Lett       Date:  2015-04-14       Impact factor: 6.005

Review 2.  Synthetic studies of viridiofungins, broad-spectrum antifungal agents and serine palmitoyl transferase inhibitors.

Authors:  Naoya Kumagai; Masakatsu Shibasaki
Journal:  J Antibiot (Tokyo)       Date:  2017-09-27       Impact factor: 2.649

3.  TiCl4-promoted tandem carbonyl or imine addition and Friedel-Crafts cyclization: synthesis of benzo-fused oxabicyclooctanes and nonanes.

Authors:  Arun K Ghosh; Cuthbert D Martyr; Chun-Xiao Xu
Journal:  Org Lett       Date:  2012-04-04       Impact factor: 6.005

4.  FeCl3-Catalyzed Tandem Prins and Friedel-Crafts Cyclization: A Highly Diastereoselective Route to Polycyclic Ring Structures.

Authors:  Arun K Ghosh; Chad Keyes; Anne M Veitschegger
Journal:  Tetrahedron Lett       Date:  2014-07-23       Impact factor: 2.415
  4 in total

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